1. Three (2 regular and one valet, which does everything but open the glove compartment. This makes my car sound fancy but I assure you it is not).

2. Yes

3. 2 cars, his car only has one key but we never swap (he very rarely takes my car but I can't drive his because it's a stick. He was teaching me for awhile and I got okay, but that was a couple years ago).

ETA: Inspired by the family I babysit for who swap cars all the time but only have one key and today was he second time the key went missing. They had to borrow my car.